Turns out the issue with the robot was the shit G code generation done in the app under windows. Another reason I avoid windows at all costs.

Generating the G code under a Linux OS, opening it under the app in windows is a functional work around for now. Generating G code for the images under windows adds weird functions to the start of the code, freaking the robot out. Despite doing it all within the robot's native app on both OS's, I've decided that Windows must be missing a dependency and I have no idea what it is. Linux will go 'Hey, I see you're after this package, in order for it to run you need these too, I'll go ahead and install them for you" Thanks Linux

​The remaining issue of drawing size stems from my poor math, and this is why: